HUE025487T2 - Process for the preparation of 2-thiohistidine and its analogs - Google Patents
Process for the preparation of 2-thiohistidine and its analogs Download PDFInfo
- Publication number
- HUE025487T2 HUE025487T2 HUE10761023A HUE10761023A HUE025487T2 HU E025487 T2 HUE025487 T2 HU E025487T2 HU E10761023 A HUE10761023 A HU E10761023A HU E10761023 A HUE10761023 A HU E10761023A HU E025487 T2 HUE025487 T2 HU E025487T2
- Authority
- HU
- Hungary
- Prior art keywords
- mixture
- formula
- acid
- compound
- add
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 21
- 230000015572 biosynthetic process Effects 0.000 title description 7
- 238000003786 synthesis reaction Methods 0.000 title description 7
- 239000000203 mixture Substances 0.000 claims description 52
- 239000002253 acid Substances 0.000 claims description 38
- 150000001875 compounds Chemical class 0.000 claims description 35
- 238000006243 chemical reaction Methods 0.000 claims description 24
- 150000003839 salts Chemical class 0.000 claims description 17
- 238000002360 preparation method Methods 0.000 claims description 8
- 230000000694 effects Effects 0.000 claims description 6
- 125000004429 atom Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 239000004575 stone Substances 0.000 claims 3
- 230000001926 lymphatic effect Effects 0.000 claims 2
- 102000018832 Cytochromes Human genes 0.000 claims 1
- 108010052832 Cytochromes Proteins 0.000 claims 1
- 206010023644 Lacrimation increased Diseases 0.000 claims 1
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 claims 1
- 230000002378 acidificating effect Effects 0.000 claims 1
- 150000001298 alcohols Chemical class 0.000 claims 1
- 238000000137 annealing Methods 0.000 claims 1
- 210000004204 blood vessel Anatomy 0.000 claims 1
- 238000005266 casting Methods 0.000 claims 1
- 125000000950 dibromo group Chemical group Br* 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 206010016531 fetishism Diseases 0.000 claims 1
- 239000000017 hydrogel Substances 0.000 claims 1
- 230000004317 lacrimation Effects 0.000 claims 1
- 210000004185 liver Anatomy 0.000 claims 1
- 229910052711 selenium Inorganic materials 0.000 claims 1
- 239000011669 selenium Substances 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- 238000003756 stirring Methods 0.000 description 20
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 16
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 16
- 229910052794 bromium Inorganic materials 0.000 description 16
- 150000003573 thiols Chemical class 0.000 description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 description 14
- 239000000047 product Substances 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 11
- 235000018417 cysteine Nutrition 0.000 description 11
- 239000007787 solid Substances 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 8
- 229910052739 hydrogen Inorganic materials 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 150000001944 cysteine derivatives Chemical class 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
- 238000003776 cleavage reaction Methods 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 238000001816 cooling Methods 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 238000005580 one pot reaction Methods 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 241001245789 Goodea atripinnis Species 0.000 description 3
- 235000011114 ammonium hydroxide Nutrition 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 230000000717 retained effect Effects 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 206010041235 Snoring Diseases 0.000 description 2
- 244000245420 ail Species 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 230000001143 conditioned effect Effects 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 235000005911 diet Nutrition 0.000 description 2
- 230000000378 dietary effect Effects 0.000 description 2
- -1 esfsyi Chemical group 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 230000007717 exclusion Effects 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 229910001369 Brass Inorganic materials 0.000 description 1
- OWNRRUFOJXFKCU-UHFFFAOYSA-N Bromadiolone Chemical compound C=1C=C(C=2C=CC(Br)=CC=2)C=CC=1C(O)CC(C=1C(OC2=CC=CC=C2C=1O)=O)C1=CC=CC=C1 OWNRRUFOJXFKCU-UHFFFAOYSA-N 0.000 description 1
- 101100174180 Caenorhabditis elegans fos-1 gene Proteins 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- UNPLRYRWJLTVAE-UHFFFAOYSA-N Cloperastine hydrochloride Chemical compound Cl.C1=CC(Cl)=CC=C1C(C=1C=CC=CC=1)OCCN1CCCCC1 UNPLRYRWJLTVAE-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 244000182067 Fraxinus ornus Species 0.000 description 1
- MAJYPBAJPNUFPV-BQBZGAKWSA-N His-Cys Chemical compound SC[C@@H](C(O)=O)NC(=O)[C@@H](N)CC1=CN=CN1 MAJYPBAJPNUFPV-BQBZGAKWSA-N 0.000 description 1
- 239000004201 L-cysteine Substances 0.000 description 1
- 235000013878 L-cysteine Nutrition 0.000 description 1
- 241000461847 Lenax Species 0.000 description 1
- 241001067739 Lotis Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 101100365384 Mus musculus Eefsec gene Proteins 0.000 description 1
- 241000219492 Quercus Species 0.000 description 1
- 206010039509 Scab Diseases 0.000 description 1
- 241000270295 Serpentes Species 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 208000002474 Tinea Diseases 0.000 description 1
- 241000130764 Tinea Species 0.000 description 1
- 241000566576 Tyto Species 0.000 description 1
- 101100108191 Vibrio parahaemolyticus serotype O3:K6 (strain RIMD 2210633) add gene Proteins 0.000 description 1
- 235000018936 Vitellaria paradoxa Nutrition 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 210000003056 antler Anatomy 0.000 description 1
- 230000003796 beauty Effects 0.000 description 1
- 229910052614 beryl Inorganic materials 0.000 description 1
- 239000010951 brass Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 230000009089 cytolysis Effects 0.000 description 1
- 239000002781 deodorant agent Substances 0.000 description 1
- 239000007854 depigmenting agent Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 235000019256 formaldehyde Nutrition 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000033001 locomotion Effects 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- RSMUVYRMZCOLBH-UHFFFAOYSA-N metsulfuron methyl Chemical compound COC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(C)=NC(OC)=N1 RSMUVYRMZCOLBH-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- DDBREPKUVSBGFI-UHFFFAOYSA-N phenobarbital Chemical compound C=1C=CC=CC=1C1(CC)C(=O)NC(=O)NC1=O DDBREPKUVSBGFI-UHFFFAOYSA-N 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 235000013616 tea Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/84—Sulfur atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0956968A FR2950890B1 (fr) | 2009-10-06 | 2009-10-06 | Procede de synthese de la 2-thiohistidine et analogues |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HUE025487T2 true HUE025487T2 (en) | 2016-04-28 |
Family
ID=41664356
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HUE10761023A HUE025487T2 (en) | 2009-10-06 | 2010-10-06 | Process for the preparation of 2-thiohistidine and its analogs |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US8835477B2 (https=) |
| EP (1) | EP2486019B1 (https=) |
| JP (1) | JP5731515B2 (https=) |
| KR (1) | KR101773995B1 (https=) |
| CN (1) | CN102596915B (https=) |
| AU (1) | AU2010305397B2 (https=) |
| BR (1) | BR112012007944A2 (https=) |
| CA (1) | CA2776833C (https=) |
| ES (1) | ES2540279T3 (https=) |
| FR (1) | FR2950890B1 (https=) |
| HU (1) | HUE025487T2 (https=) |
| IN (1) | IN2012DN03819A (https=) |
| RU (1) | RU2548153C2 (https=) |
| WO (1) | WO2011042478A1 (https=) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR3021655B1 (fr) | 2014-05-30 | 2016-07-08 | Tetrahedron | Nouveaux composes de type 5-acylsulfanyl-histidine en tant que precurseurs des 5-sulfanylhistidines correspondantes et de leurs disulfures |
| JP6864131B1 (ja) * | 2020-03-04 | 2021-04-28 | 長瀬産業株式会社 | Ｌ−エルゴチオネイン含有組成物 |
| US20240199687A1 (en) * | 2021-04-22 | 2024-06-20 | University Of Vermont And State Agricultural College | Substitution of histidine with 2-thiohistidine in bioactive peptides |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2707087B1 (fr) * | 1993-06-28 | 1995-10-13 | Bioxytech | Nouveau procédé de préparation de l'ergothionéine. |
| FR2714380B1 (fr) * | 1993-12-24 | 1996-05-24 | Bioxytech | Utilisation de dérivés 2-mercapto-imidazole substitués en position 4 (ou 5) comme agents antioxydants, leur procédé de préparation et leurs applications en pharmacie, cosmétique ou alimentaire. |
| ES2194209T3 (es) * | 1996-07-22 | 2003-11-16 | Monsanto Co | Inhibidores de metaloproteasa de tiol sulfona. |
| AU2002211666A1 (en) * | 2000-10-11 | 2002-04-22 | Esperion Therapeutics, Inc. | Sulfide and disulfide compounds and compositions for cholesterol management and related uses |
| US7767826B2 (en) * | 2007-10-05 | 2010-08-03 | Pharmatech International, Inc. | Process for the synthesis of L-(+)-ergothioneine |
| FR2950889B1 (fr) | 2009-10-06 | 2011-11-18 | Tetrahedron | Procede de synthese de l'ergothioneine et analogues |
-
2009
- 2009-10-06 FR FR0956968A patent/FR2950890B1/fr not_active Expired - Fee Related
-
2010
- 2010-10-06 CA CA2776833A patent/CA2776833C/fr not_active Expired - Fee Related
- 2010-10-06 AU AU2010305397A patent/AU2010305397B2/en not_active Ceased
- 2010-10-06 US US13/500,887 patent/US8835477B2/en not_active Expired - Fee Related
- 2010-10-06 CN CN201080047020.4A patent/CN102596915B/zh not_active Expired - Fee Related
- 2010-10-06 EP EP10761023.0A patent/EP2486019B1/fr not_active Not-in-force
- 2010-10-06 HU HUE10761023A patent/HUE025487T2/en unknown
- 2010-10-06 WO PCT/EP2010/064947 patent/WO2011042478A1/fr not_active Ceased
- 2010-10-06 ES ES10761023.0T patent/ES2540279T3/es active Active
- 2010-10-06 RU RU2012117977/04A patent/RU2548153C2/ru active
- 2010-10-06 JP JP2012532584A patent/JP5731515B2/ja not_active Expired - Fee Related
- 2010-10-06 KR KR1020127011714A patent/KR101773995B1/ko not_active Expired - Fee Related
- 2010-10-06 IN IN3819DEN2012 patent/IN2012DN03819A/en unknown
- 2010-10-06 BR BR112012007944A patent/BR112012007944A2/pt not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| CN102596915A (zh) | 2012-07-18 |
| JP5731515B2 (ja) | 2015-06-10 |
| BR112012007944A2 (pt) | 2015-09-22 |
| EP2486019A1 (fr) | 2012-08-15 |
| RU2012117977A (ru) | 2013-11-20 |
| FR2950890A1 (fr) | 2011-04-08 |
| KR20120100977A (ko) | 2012-09-12 |
| WO2011042478A1 (fr) | 2011-04-14 |
| CA2776833C (fr) | 2019-03-19 |
| JP2013506705A (ja) | 2013-02-28 |
| ES2540279T3 (es) | 2015-07-09 |
| AU2010305397B2 (en) | 2014-07-10 |
| CA2776833A1 (fr) | 2011-04-14 |
| KR101773995B1 (ko) | 2017-09-01 |
| IN2012DN03819A (https=) | 2015-08-28 |
| US8835477B2 (en) | 2014-09-16 |
| CN102596915B (zh) | 2016-04-20 |
| AU2010305397A1 (en) | 2012-05-24 |
| RU2548153C2 (ru) | 2015-04-20 |
| EP2486019B1 (fr) | 2015-03-25 |
| FR2950890B1 (fr) | 2011-12-30 |
| US20120330029A1 (en) | 2012-12-27 |
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